Holiday rentals in Woodland Park

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Top-rated holiday rentals in Woodland Park

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Guest favourite

Tiny home in Woodland Park

4.93 out of 5 average rating, 139 reviews

Free parking 2-BR Tiny Home w/Jacuzzi & BBQ grill

- Experience tranquility at this exclusive Tiny home, nestled near the breathtaking Rocky Mountains - Unplug from chaos and reconnect with nature and loved ones while enjoying surrounding views - For those seeking personal growth, Aspen Counseling & Education is nearby - Conveniently located just minutes from Shining Mountain Golf Course, Woodland Fitness Center and Memorial Park, you’ll have easy access to outdoor activities like hiking and picnicking - Book your stay today and discover comfort

Guest favourite

Home in Woodland Park

4.95 out of 5 average rating, 130 reviews

Little Woody's Hideaway-(4)DownTown,HotTub,pets

Cozy little 2 story home with 1 bedroom, 1 bath with a pull out sofa sleeper in the center of downtown Woodland Park. It has so much charm you will never want to leave! You have shops and restaurants a hop skip and jump away and the memorial park in your backyard and you can walk to almost EVERYTHING. You will enjoy the farmers market in the spring and summer that is a block away or sit outside and BBQ. Beautiful hikes are 5-20 mins away, we have a guide at the hideaway for all your adventures!

Guest favourite

Guest house in Woodland Park

4.96 out of 5 average rating, 111 reviews

Rose Mountain Escape Pet friendly W/pet fee

Rose Mountain escapes has beautiful views of Aspen trees. Located 5 miles from Charis,, 15 mins from downtown Woodland Park & 2hrs from Breckinridge, 2 blocks from BLM land allows ATVs, Motor/Mountain bikes and walks through the forest. It is a small cabin with a VERY STEEP STAIRCASE to the bedroom. We have a large deck with Adirondack chairs, a gas fire pit and grill for your use. We have great WiFI. We have kitchenette, washer and dryer. Pet friendly with CLEANING FEE list pet on reservation!

Guest favourite

Tiny home in Woodland Park

4.94 out of 5 average rating, 166 reviews

Boutique TinyHome w/Direct View of PikesPeak!

If mountain views are what you want, you have found your get away with DIRECT unobstructed views of world famous Pike's Peak. This one of a kind cozy tinyhouse is nestled in a lovely Tiny home community called Peak View Park and is surrounded by breathtaking mountain views located in Woodland Park. Close to great restaurants and a variety of grocery stores. Woodland Park is located just 20 minutes west of Colorado springs on Highway 24. Come and experience the “City above the Clouds”.

Guest favourite

Cabin in Cascade-Chipita Park

4.99 out of 5 average rating, 106 reviews

Classic Colorado mountain cabin

Take it easy at this unique and tranquil getaway. A family cabin crafted in the 1940s, unchanged with the exception of tastefully done upgrades and improvements. Authentic western decor and knotty pine interior. Easy access to nearby hiking and attractions. Minutes from the beautiful small mountain towns of Green Mountain Falls, Manitou Springs and Woodland Park. Local attractions including Pikes Peak, North Pole Santa’s Workshop, Cripple Creek, Garden of the Gods are just minutes away.

Guest favourite

Guest suite in Woodland Park

5 out of 5 average rating, 231 reviews

Private Guest Suite w/Trees & Awesome Peak Views

Picture-perfect Pikes Peak views from your living room, bedroom, and covered patio of this stunning Colorado mountain home's guest suite with a classic Colorado feel. The suite includes the entire walk-out lower-level of our home. It is private, separate, and has its own entrance. With a full kitchen and central location, this is the perfect base-camp for a Colorado get-away; however, with the Ponderosa Pine, Aspen, and hiking trails right up the street, you may not want to ever leave.

Guest favourite

Townhouse in Woodland Park

4.9 out of 5 average rating, 202 reviews

Westwood Mountain Retreat!

Looking for the perfect escape? This spacious townhome is the perfect place to relax and unwind in Woodland Park. Equipped with a queen bed and pullout futon, this townhome is great for couples and small families. A perfect home base to venture out for nearby trails for hiking, fly fishing, and a five minute walk to Charis Bible College. Within an hours drive to Pike's Peak. A short 5 minute drive to downtown Woodland Park for shopping and dining and 30 minutes from Colorado Springs.

Guest favourite

Guest suite in Woodland Park

5 out of 5 average rating, 117 reviews

Country Ridge Retreat - private guest suite

Enjoy this private, peaceful mountain guest suite walking distance from a National Forest trail. It's a 5 min. drive to downtown Woodland Park for dining or swimming at the Aquatic Center. Drive 30 min. east and you have access to all Colorado Springs has to offer including Cheyenne Mountain Zoo, Garden of the Gods, Old Colorado City, Pikes Peak and Manitou. Drive 30 min. west and you have access to State Parks, countless hiking trails, Rampart Reservoir & skiing is just a day trip away!

Guest favourite

Cabin in Woodland Park

4.96 out of 5 average rating, 189 reviews

The Potlatch Cabin

This cozy mountain hideaway is all within an hours drive or less to Pikes Peak, hiking, fishing, Garden of the Gods, Seven Falls, snowshoeing, cross country skiing, ATV and snowmobile trails, Manitou Springs, breweries, coffee shops, shopping, wine tasting and more. Relax on the front porch and enjoy the wildlife or stars. Games and books available in the cabin or snuggle by the fireplace and watch movies on the large flat screen smart television. There are 3 steps down into bathroom.

Guest favourite

Tiny home in Woodland Park

4.92 out of 5 average rating, 439 reviews

Wabi Sabi Tiny House - No Cleaning Fees!

I designed and built this Tiny House a few years ago! As such, it's still an ongoing work in progress and so not quite as picturesque as the finished homes you may see on TV, but it's still fully functional, cozy, and homey. To sleep, you'll have the choice of a queen size loft bed (must climb stairs to access) or a queen size (comfortable!) sofa bed on the ground floor. Located in Woodland Park, CO you have an AMAZING view of Pike's Peak and close proximity to so many adventures 🤗

Guest favourite

Tiny home in Woodland Park

4.9 out of 5 average rating, 264 reviews

Spacious Tiny House - with A/C!

Unplug from the hustle and bustle as you wake up to the rustling of leaves and the crisp mountain air. But don't worry about roughing it-our tiny home is strategically situated near local shops, eateries, and markets, ensuring you have everything you need just a stone's throw away. After a day of exploring rugged trails and capturing awe-inspiring vistas, unwind in a space that boasts modern comforts like hot showers, comfortable bedding, and Wi-Fi connectivity.

Guest favourite

Cabin in Woodland Park

4.97 out of 5 average rating, 220 reviews

Lil Lincoln

The Lil Lincoln sits at an elevation of 9,560ft. and was originally built on the Western Slope of Colorado in the 50’s and was moved in 1965 to it’s current location near Woodland Park. The story behind the move was that a doctor moved his practice in 1959 to Woodland Park. He wanted his nurse to join him, she said she'd move if he moved her cabin. Well he did, and so did she.